Oxime-containing carboxylate compound and use thereof

A technology for ester compounds and carboxylic acids, applied in the fields of chemicals, applications, organic chemistry for biological control, and can solve problems such as herbicide resistance

Active Publication Date: 2015-07-29
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to develop new herbicides to solve the increasingly serious problem of herbicide resistance, the invention provides an oxime-containing carboxylate compound and its use

Method used

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  • Oxime-containing carboxylate compound and use thereof
  • Oxime-containing carboxylate compound and use thereof
  • Oxime-containing carboxylate compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0170] Example 1 Preparation of Compound 16

[0171]

[0172] 1) Preparation of intermediate (IV-1)

[0173] Add 69g (1mol) of triazole to a 1000mL three-neck bottle filled with 300mL of DMF, add 165.6g (1.2mol) of potassium carbonate, slowly add 134.5g (1mol) of chloropinacolone dropwise, stir at room temperature, and slowly Raise the temperature to 80°C and react for 4 hours. After the reaction is monitored by liquid chromatography, add 500mL of water, extract with 150mL×3 ethyl acetate, and dry the organic layer to obtain 120g of intermediate (IV-1). The product is a yellow solid . It was directly used in the next step without purification.

[0174] 2) Preparation of intermediate (III-1)

[0175] Weigh 0.83g (0.036mol) of sodium metal, cut it into sodium wire and put it into a reaction bottle filled with 50mL of ethanol in batches. After the sodium wire is completely reacted, raise the temperature to 80°C and reflux until no bubbles are released. Put the reaction sol...

Embodiment 2

[0179] Example 2 Preparation of Compound 23

[0180]

[0181] 1) Slowly add 3.6g (0.01mol) of acid (II-2) into a two-necked bottle containing 100ml of thionyl chloride, add 2 drops of DMF, heat to reflux until the solution is clear, continue heating for 1h, and evaporate under reduced pressure Excess thionyl chloride yielded 3.8 g of intermediate (II-2) as a colorless oil.

[0182] 2) According to the method described in step 4) of Example 1, 0.6 g of compound was prepared by reacting 1.0 g (0.0028 mol) of intermediate (II-2) with 0.5 g (0.0028 mol) of intermediate (III-1) (23), yellow oil. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δppm1.30(9H,s), 7.11-7.17(2H,m), 7.33(2H,d), 7.67(1H,d), 7.84(1H,s), 8.25(1H,d), 8.91(1H ,s).

Embodiment 3

[0183] Example 3 Preparation of Compound 26

[0184]

[0185] 1) According to the method described in step 1) of Example 2, the acid of (II-2) was replaced by the acid of (II-3) to obtain the intermediate (II-3) as a colorless oil.

[0186] 2) According to the method described in step 4) of Example 1, 1.0 g (0.005 mol) of intermediate (II-3) was reacted with 1.0 g (0.005 mol) of intermediate (III-1) to obtain 1.3 g of compound (26), white solid, melting point 141.0°C. 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 ) δppm 1.42 (9H, s), 2.29 (3H, s), 4.14 (3H, s), 8.09 (1H, s), 9.32 (1H, s).

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Abstract

The invention belongs to the field of agricultural herbicides, and concretely relates to an oxime-containing carboxylate compound and a use thereof. The oxime-containing carboxylate compound is represented by general formula (I), has very good weeding activity, can effectively control barnyard grass, piemarker, setaria viridis, Zinnia elegans and other weeds, realizes a very good weeding effect under a low dosage, is highly safe to crops, is especially safe to corn and rice (post-emergence), and can be used as a herbicide in the agricultural field.

Description

technical field [0001] The invention belongs to the field of agricultural herbicides, and in particular relates to an oxime-containing carboxylate compound and its application. Background technique [0002] Patent DE3005899 discloses the following compound A and compound B (numbered as compound 5 and compound 8 in the patent) with fungicidal activity. [0003] [0004] Compound C (cas: 302602-89-7), no specific references disclosed. [0005] [0006] In the prior art, the compound represented by the general formula (I) of the present invention and its herbicidal activity have not been reported. Contents of the invention [0007] In order to develop new herbicides to solve the increasingly serious problem of herbicide resistance, the invention provides an oxime-containing carboxylate compound and uses thereof. [0008] To achieve the above object, the technical solution adopted in the present invention is: [0009] Technical scheme of the present invention is as fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C07D249/08C07D401/14C07D231/12A01N43/653A01N43/56A01P13/00
Inventor 吴峤杨吉春马宏娟张静静崔东亮关爱莹刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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